Process for dyeing polyester textiles

ABSTRACT

PROCESS FOR DYEING OR OPTICALLY BRIGHTENING CELLULOSE TRIACETATE AND AROMATIC POLYESTER TEXTILE MATERIALS WHICH COMPRISES TREATING SAID TEXTILE MATERIALS WITH A DISPERSION OF A DYESTUFF OR OPTICALLY BRIGHTENING AGENT WHICH CONTAINS AT LEAST ONE OPTIONALLY SUBSTITUTED CARBONAMIDO OR SULPHONAMIDO GROUP IN A HALOGENATED HYDROCARBON AND IN THE PRESENCE OF A SMALL AMOUNT OF WATER, THE SAID TREATMENT BEING CARRIED OUT AT A TEMPERATURE ABOVE THE BOILING POINT OF THE AZEOTROPE OF THE HALOGENATED HYDROCARBON AND THE WATER, AND AT A PRESSURE ABOVE ATMOSPHERIC PRESSURE.

United States Patent 3 748 091 PROCESS FOR uYEnsG lOLYESTER TEXTILESDavid Melville Fawkes, Manchester, England, assignor to ImperialChemical Industries Limited, London, England N0 Drawing. Filed Apr. 7,1971, Ser. No. 132,183

3,748,091 Patented July 24, 1973 h tile materials, it is preferred togive the dyed textile mate- Claims priority, applicatlion2 GreatBritain, Apr. 22, 1970,

/7o Int. (:1. D06p 1/20 US. Cl. 8-39 6 Claims ABSTRACT OF THE nrscLosUnathe presence of a small amount of water, the said treatment beingcarried out at a temperature above the boiling point of the azeotrope ofthe halogenated hydrocarbon and the Water, and ate pressure aboveatmospheric pressure. i

This invention relates to an improved process for the dyeing or opticalbrightening of cellulose triacetate and aromatic polyester textilematerials and their blends with other textile materials.

It has previously been proposed to dye or optically brighten synthetictextile materials at elevated temperatures with solutions or dispersionsof water insoluble dyestuffs or optically brightening agents in achlorinated-hydrocarbon solvent, especially perchloroethylene,optionally containing small amounts of water, the said treatment beingoptionally carried out at pressure above atmospheric pressure. Thisprocess suffers from the disadvantage that the affinity of the saiddyestuffs or optically brightening agents is low, so' that only paleshades can be achieved by this process. a

(It has now been found that aparticularly valuable class of dyestuffs oroptically brightening agents which can be used are those which areinsoluble or only slightly soluble in the chlorinated hydrocarbon andwhich contain at least one optionally substituted carbonamido (CONH orsulphonamido (SO NH groupv as, under these particular methods ofapplication, this class of dyestuffs or optically brightening agents hasa much higher afiinity an improved process for dyeing or opticallybrightening cellulose triacetate and aromatic polyester textile materiala treatment in a clearing bath comprising an emulsion of an aqueousalkaline solution of sodium hydrosulphite in perchloroethylene.

The amount of water present in the dyeing process is preferably between0.2% and 5% based on the volume of the halogenated hydrocarbon.

Although the dyeing process is carried out at a temperature above theboiling point of the azeotrope of the halogenated hydrocarbon and thewater, it is preferred that the temperature be equal to or greater thanthe boiling point of the pure halogenated hydrocarbon.

As examples of halogenated hydrocarbons which can be used in the processof the invention either singly or in the form of mixtures there may bementioned chloroform, carbon tetrachloride, dibromoethylene,trichloroethylene, 1:l:Z-trichloro-lz2z2-trifiuoroethane, 1:1:1trichloroethane, and preferably tetrachloroethylene, (perchloroethylene).

There can also be present emulsifying agents which can be anionic,cationic or non-ionic. Non-ionic emulsifying agents may be, for example(a) polyethers of hydroxy,

mercapto and amino compounds such as polyalkoxy-fatty alcohols,polyalkoxy polyols, polyalkoxy-mercaptans,

polyalkoxy aliphatic amines, polyalkoxy alkylphenols,

face Active Agents by Elworthy, Florenceand Macfar lane, published 'byChapman and Hall Ltd., in 1968.

The dyestuffs and optical brightening agents which can be used in theprocess of the invention can be of any of the recognised classes ofdyestuffs, for example, methine, styryl, phthalocyanine,phthaloperinone, quinphthalone, azo, anthraquinone and nitro dyestuffs,and optical brightening agents, for example stilbenes, coumarins,pyrazolines, naphthalimides, carbostyryls, 1:3:4 oxodiazoles,

rials which comprises treating said textile materials with w adispersion of a dyestuif or optically brightening agent which containsat least one optionally substituted carbonamido or sulphonamido group ina halogenated hydrocarbon and in the presence of a small amount ofwater,-

the said treatment being carried out at a temperature above the boilingpoint of the azeotrope of the halogenated hydrocarbon and the water, andat a pressure above atmospheric pressure.

The process of the invention can be conveniently carried out byimmersing the textile material in a dispersion of v the said dyestuif oroptical brightening agent in the haloof the azeotrope of the halogenatedhydrocarbon and the water. At the conclusion of the process the dyed oroptically brightened textile material may be rinsed with the brighteningagent or is attached thereto through an alkylene or an alkyleneaminoradical. Such groups can be conveniently represented by the formula:

wherein X represents '-CO or -SO and R and R each independentlyrepresent a hydrogen atom or an optionally substituted alkyl,cycloalkyl, aryl or heterocyclic radical, or R and R are joined togetherto form with 3 4 the nitrogen atom N a 5- or -6-memberednitrogen-conparts of perchloroethylene in the presence of 0.1 part,taining heterocyclic ring. as deflocculating agent, of the polyureaproduct prepared As examples of the radicals represented by R and R asdescribed below. 2 parts of water are added, the mixthere are mentionedlower alkyl such as methyl, ethyl, ture is placed in a deying vessel and20 parts of polyethylpropyl and butyl, substituted lower alkyl forexample hy- 5 one terephthalate textile material in the form of stapledroxy lower alkyl such as fi-hydroxyethyl, lower alkoxy cloth isimmersed in the mixture. The dyeing vessel is then lower alkyl such asfi-methoxyethyl and 'y-methoxypropyl, sealed and heated at 120 C., for30 minutes to effect dyecyano lower alkyl such as fi-cyanoe hyl, aryl Sus it e ing. The dyed textile material is then removed from the loweralkyl such as benzyl, cyclohexyl, optionally substipressure vessel,rinsed in acetone to remove the excess dyetllted P 3 Such as P y itselfand tolyl, y Chlo- 10 bath liquor and any loosely bound dyestufl, and isfinally rophenyl and bromophenyl. dried. The textile material is therebycoloured a deep yel- AS examples of the atld fi-membefed nitfogelPcOH-lowish-orange shade of excellent fastness properties. mininghetefocyclic Tings formed y lointflg together R1, The polyurea productused in the above example was it R and the nitrogen atom N there may bementioned lf b i d as f llows; Py indolinfi, Piperidine, morpholine,PiPeYaZine A solution of 73.7 parts of a commercially available andN-alkylpiperazine. 40% solution in butyl acetate of polymerised mixed2:4- It is however Pmtermt1 that R1 and R2 each represent and2:6-tolylenediisocyanates containing 5.7% of isocyaa hydrogen atom. nategroups and less than 0.5% of free tolylene diisocya- The Said dyestutfsand Optical bl'ightehing agehts can nate in 32 parts of acetone wasadded to a stirred soluthemselves be Obtalhed y any of the Convehhohalmath tion of 53.5 parts of a fatty secondary amine derived from Dds 0 Pg dyestutf? i oPticatbl'ightehihg {agents soya and commerciallyavailable under the trade name from intermediates containing the sa1dcarbonam1de or Armeen is a registered trademark) in 11 P F E t h r gmggdg fg g gf i ga2 parts of acetone at 50 to 55 C. The acetone was thengroups 111 0 e P e P YP removed by distillation under reduced pressure.

include for exam le:

(a) Treating a dyestuif or optical brightening agent 25 In Place of thedyestuff s d in Example 1 ther e with chlorosulphonic acid and reactingthe resulting suldyestuffs obtained by dlazohslhg the phonchloride withthe appropriate amine amines listed in the second column of thefollowing table (b) Reacting a dyestuif or optical brightening agent hcohphng the reuttlllg dlflZO f P S mm the 0011- containing a carboxylicacid group or groups with thionyl P components llsted 111 rd 60 1111111of the table.

chloride and treating the resulting acid chloride with the The fourth olmn 0f the table lists the shades of the appropriate amine. resultingdyeings.

Example Amine Coupling component shade 4- nob nzene sul honamide.-. N:N-i(flhy r xy hyl)aniline-.-..- Yellowidh-oran e. i e pN-methyl-N-(fi-hydroxyethyDaniline. Do. g 4 dN-methyl-N-(fl-eyanoethyl)aniline..- Yellow. 5 doN-ethyl-N-(fl:v-dihydroxyprcpybanili Yellowish-orange. 6 taminolgenzeneea{bgnarnbixdgs.find-r. .15.33... Nzbgdi(5-hydroxyethyl)-mrt0lu1d1ne Do.

7-.. amino enzene so onoxye y am a o.

8 2-ehloro-4-nitroanilihe "Y 3-sulphonamido-N:N-didthydroxyethybanilineBluish-red.

(c) Reacting together intermediates which give a dye- EXAMPLE 9 stulf oroptical brightening agent (for example a diazo OJ part of the monoazodyestuff obtained by coupling component and a coupling component) atleast one of which contains a carbonamide or sulphonamido group.

The dispersion of the dyestuff or optical brightening agent in thehalogenated hydrocarbon can be conveniently obtained by milling orgrinding the dyestufi or optical brightening agent in the halogenatedhydrocarbon in the presence of a defiocculating agent. As deflocculatingagents there may be mentioned, for example, polyureas which areessentially free from basic amino groups and which contain at least twourea groups and at least two groups each of which is an alkyl, alkenylor alkapolyenyl group containing at least eight carbon atoms, and whichare soluble in organic solvents.

The cellulose triacetate and aromatic polyester, espe- 1y bound dyestufiand 15 then dried A deep yellow shade cially polyethyleneterephthalate,textile materials can be of excellent fastness Properties is therebyobtainedin the form of fibres or filaments or knitted or woven EXAMPLE1() oods. If desired the said textile materials can be in the v f orm ofblends with other textile materials particularly gg g ifig ggfii g3331352 3 55 gif cotton and woollen textlle materials diazotised3-chloro-4-aminobenzenesulphonamide with N- When applied to synthetictextile materials by the prOcmethyl-N-(fl-cyanoethyl)aniline, and thedyemg 18 then ess of the 1nvent1on the said dyestuffs and optical brightcarried out for 3 0 minutes at 120 C. A p orange y ening agents haveexcellent afiinity thus enabling heavy depths of shades to be obtained,and the resulting dyed mg of excellent fastness propertles Obtamed' oroptically brightened textile materials have excellent EXAMPLE 11 i tothe tests commonly applied to Such textile 0.1 part of the dyestufiobtained by coupling diazotised ma 4-aminobenzenesulphonamide withN-methyl-N- -c ano- 1 i mventlfn fif fi g notdhmltedtby theethyl)aniline is dispersed in 320 parts of perchlorh th y lene Y es m wc t a par 8 an Percen ages are Y containing 0.05 part of the polyureadescribed in Example welght' EXAMPLE 1 1. 2 parts of water are added,the mixture placed in a dyeing vessel and 20 parts of cellulosetriacetate fabric are 0.2 part of the monoazo dyestufi obtained bycoupling immersed in the liquid. The vessel is sealed and dyeingdiazotised 4-aminobenzenesulphonamide with N-ethyl-N- carried out for 30minutes at C. The dyed material is (p-hydroxyethynaniline is dispersedby milling in 800 75 then removed from the dyebath, rinsed in aqueousethanol,

diazotised 4-aminobenzenesulphonamide with N:N-di(;3- cyanoethyl)anilineis dispersed by milling in 320 parts of perchloroethylene containing0.05 part of the polyurea obtained as described in Example 1 above. 2parts of water are then added, and the resulting mixture placed in adyeing vessel. 20 parts of a polyester fibre which is commerciallyavailable under the trade name of Crimplene (Crimplene is a registeredtrademark) are then immersed in the mixture, the dyeing vessel issealed, and dyeing then carried out for 30 minutes at C. The dyedtextile material is then removed from the vessel, rinsed in acetone toremove excess dyebath liquor and any looseand is dried. A deep yellowshade of excellent fastness properties is obtained.

The following table gives further examples which illustrate theinvention, the dyestuff used in Example 10 being replaced by thedyestuffs obtained by diazotising the amines listed in the second columnof the table and coupling with the coupling components listed in thethird column of the table. The fourth column of the table gives theshades of the resulting dyeings.

wherein X represents --SO and R and R each independently representhydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl orcyano lower alkyl in a halogenated hydrocarbon and in the presence ofbetween 0.2% and 5% water based on the volume of the halogenatedhydrocarbon, said treatment being carried out at a temperature above theboiling point of the azeotrope of the halogenated hydrocarbon and theWater, and at a pressure above atmospheric pressure.

Example Amine 12 4-amgnobenzeuesulphonamide 143-nitro-4-aminobenzensulphonamide N-rnethyl-N-(fi-cyanoethyl)aniN:N-di(fl-cyanoethyl)aniline3-chlor0-4-aminobenzenesulphon-N-(fi-chloroethyDami e d4-aminobanzensulphon-N-(B-chloroethyl)amide 2-amino-5-nitrobenzamideCoupling component 1-ethyl-3-eyano-4-methy1 6-hydroxypyrid-2'0neN-methyl-N-(fl-cyanoethyD-mflgoluidine.

Shade Greenish-yellow. Orange.

line

do do N-methyl-N-(B-cyanoethyl) aniline2aminobenzthiazole-fi-sulphonamide do do N :N -di (dcyanoethyl) anilinedo -m-toluidine 22 2-amino-5-nitrobenzenesulphon-N-methylamide.cyanoethyDani 'ne 23-.-. do N2N-di(fi-cyanoethybauiline 24 4-nitr ili2-naphthylamine-5-sulphonamide 25 2chloro-4-nitr do Red. 262-cyano-4-nitroaniline--- do Bluish-red. 27 2-chloro-4-nitr0am'lineZ-naphthylamineA-sulphonamide Reddish-viol'w.

do Z-Baphthylaminel-sulphon-N-(B-hydroxyethyDamide Violet.a-methoxyaniline u N-ethyl-N-(fi-carbamoylethyl)aniline Orange2-carboxy-4mtroan1l1ne N-methyl-N-(fl-carbamoyletliyl)aniline VioletZ-methylsulphonylt-nitroanilin Bluish-red. 2-cyano4-nitroaniline .do Do.33 do B-acetylamino-N-methyl-N-(B-earbamoylethyl)aniline.. Bluish-vioet. 34 2-am1no-5-mtroth1az0leN-(B-cyanoethyl)-N-(fl-carbamoylethyl)aniline-.. Blue. 352-arninohenzthiazole-(i-methylsulphoneN-ethyl-N-(B-carbamoylethyl)-m-t0luidine Red. 36 -mtrnanilmaN-methybN-(Bsulphamoylethyl) aniline. Red.

N-ethyl-N-(B-sulphamoylethyl)-m-toluidine Bluish-re'l. 382-cyano-4-n1troaniline d0 Violet. 39.. 2:4-din1tro-6-bromoaniline2-eth0xy-5-acetylamino-N-(Bsulpham0ylethyl)an1l1ne- Blue.

EXAMPLE 40 2. Process as claimed in claim 1 wherein the halo In place ofthe 0.1 part of dyestuff used in Example there is used 0.1 part of1:4-diaminoanthraquinone-Z-carbonamide or of1:4-diaminoanthraquinone-Z-carbo-N:N- di(/8-hydroxyethyl)amide or ofl-amino 4 (p-hydroxyaniline) anthraquinone 2 carbonamide wherebyreddishblue, reddish-blue and blue dyeings respectively are obtained ofexcellent fastness properties.

EXAMPLE 41 0.01 part of the fluorescent brightening agent 1:4-di-(4-carbamoylstyryl)benzene is milled in 320 parts of perchloroethylenecontaining 0.005 part of the polyurea described in Example 1. 2 parts ofwater are added, the mixture placed in a dyeing vessel, parts of anaromatic polyester fabric are added, the vessel sealed and then heatedfor minutes at 120 C. The fabric is then removed from the vessel, rinsedin perchloroethylene and dried. The fabric is brighter than theuntreated fabric.

EXAMPLE 42 genated hydrocarbon is perchloroethylene.

3. Process as claimed in claim 1 wherein the dispersion contains adeflocculating agent.

4. Process as claimed in claim 1 wherein the dispersion contains anemulsifying agent.

5. Process as claimed in claim 1 wherein the dyestuff is an azo dyestuffwhich contains at least one unsubstituted sulphonamido group directlyattached to a carbon atom of an aryl radical or attached thereto throughan alkylene or alkyleneamino radical.

6. Process as claimed in claim 1 wherein the dyestuif is ananthraquinone dyestuff which contains at least one unsubstitutedsulphonamido group directly attached to a carbon atom of an aryl radicalor attached thereto through an alkylene or alkyleneamino radical.

References Cited UNITED STATES PATENTS 3,622,558 11/1971 Kolliker et a1.850 X 3,623,834 11/1971 Seuret et a1. 8-62 X 2,725,390 11/1955 Fogelmanet a1 8-173 X 3,623,833 11/1971 Wildermuth et a1 8--40 FOREIGN PATENTS1,192,984 5/ 1970 Great Britain 8-174 1,535,352 6/1968 France 8174 OTHERREFERENCES Ciba-Geigy Review, 1971/4, pp. 11-13.-

LEON D. ROSDOL, Primary Examiner T. J. HERBERT, JR., Assistant ExaminerUS. Cl. X.R. 841 C, 174

